How to Ask Better Questions

Guest Post by Bobby Powers

Previously posted at

I thought I knew how to ask good questions until I met a guy named James.

As I began to work with James, I watched in awe as I compared his questions to my own. He used questions as a sharp-edged knife to cut through mental clutter, uncertainty, and decision paralysis. Whether we were in an all-hands meeting, a team meeting, or a 1-on-1, James knew when to broaden a discussion to include more viewpoints and when to narrow it to drive toward a decision.

For years, I had known in my gut that asking better questions was the secret to unlocking better answers, but I had struggled to find any good resources on the topic. I’d read books with promising titles like Good Leaders Ask Great Questions, but the books didn’t provide enough tactical advice to be helpful.

Over the past two years, I’ve been taking notes on what I’ve observed from James and other leaders who ask the right question at the right time. These 11 tips have helped me immensely, and I’m sure they’ll help you as well.

1. Ask one question at a time.

One of my colleagues tends to spray questions like a shotgun blast. He’ll rattle off four questions at once and leave everyone wondering what they’re supposed to answer: The first question? The last one? The one they’re most comfortable answering? All of them, if they can remember the full list?

Exercise discipline with your questions. Ask one question at a time, then move on to the next question. Doing so will lead to more robust discussion, fewer blank stares, and a more engaged decision-making process.

2. Opt for shorter questions.

“You don’t need a runway of context, justification, and general flim-flam to be curious. It’s not really about you. Save everyone the time, and just ask the question.” -Michael Bungay Stanier

Asking long questions is often as bad as asking multiple questions. Long questions confuse others. People get lost in the rambling, rollicking nature of long questions, which makes it more difficult for them to respond with useful information.

For example, which question would you rather answer?

    • “You’re a really talented person, and I think you can achieve a lot at our company. Would you be interested in taking over Terry’s job as Head Accountant or is that not something that interests you? I mean, it’s okay if you don’t want to do that…I just think you’d be a great fit, and Terry will be leaving soon so we need someone to fill that role. I know you have a lot of ambition and you’ve also talked about switching departments, so I’m not sure where exactly you want to go in your career. What do you think?”
    • “Would you be interested in stepping into the Head Accountant role when Terry leaves the company?”

It takes a surprising amount of confidence to ask shorter questions, like the second one above. Our brains want to fill in more details rather than cutting ourselves off after we’ve asked the question.

Don’t give your tongue an unnecessary workout. Ask short, simple questions.

3. Become comfortable with silence.

According to a 2018 article in Inc., most Americans feel awkward after about four seconds of silence. Many inexperienced leaders rush to fill those awkward silences with something — anything — in order to make themselves and others feel less uncomfortable.

But silence is not a bad thing. Silence is the noise thinking makes.

Silence gives people time to provide a more thoughtful answer to the question you just posed. In many situations, silence is your proof that you’ve just asked the right question.

4. Ask open-ended questions.

Open-ended questions (those that cannot be answered with a simple “yes” or “no”) give the other person full latitude to share their ideas.

In work and in life, open-ended questions provoke rich dialogue rather than one-word responses. If you’re walking out of a movie with a friend, a question like “What did you think of the movie?” elicits a much richer response than a question like “Did you like that movie?”

Similarly, asking your boss “How do you think I’ve been performing lately?” is fundamentally different than “Do you think I’ve been performing well?”

There’s nothing inherently wrong with closed-ended questions. There’s a time and place for them (as we’ll address later), but closed-ended questions tend to be more biased and limiting than open-ended questions.

5. Avoid “Why?” questions.

Questions that begin with “why” tend to make presumptions or suggest solutions (e.g., “Why did you…”, “Why wouldn’t you just…”). Those types of questions put the other person on the defensive, feeling like they need to defend a decision they’ve made or an idea they’ve suggested.

You want to invite someone into a discussion with you — not shut down the conversation with a question that makes the other person defend something.

6. Ask “What” and “How” questions.

If you took a journalism class in high school or college, you probably learned about the “5 W’s and an H”: Who, What, Where, When, Why, and How. All six of those elements are necessary when writing a story or understanding a concept at a deep level. But some of those questions yield better, fuller answers than others.

Questions that start with “What” or “How” invite the other person to share their ideas with you and the rest of the group. Here are a few examples:

    • “What’s on your mind?”
    • “What do you think we should do next?”
    • “How do you think we could accomplish that?”

7. Consider whether to widen or narrow the funnel.

“The essential skill of inquiry involves picking the right type of question for a situation. For instance, questions can go broad or deep.” — Amy Edmondson

When you’re trying to collect as many ideas as possible, you want to ask questions with a very wide funnel: more is better.

For example, if you’re running a two-hour brainstorming meeting, you probably want to begin with the premise that every idea is worth sharing. Open-ended questions lend themselves well to brainstorming because they widen the funnel, prompting wide discussion and idea generation:

    • “What might we do to improve engagement on our platform?”
    • “How could we streamline our sales process?”

But eventually, you will need to pivot to action. Maybe an hour and a half into the brainstorming meeting, you decide it’s time to force prioritization and make a few decisions. That pivot requires a different set of questions — questions that begin to narrow the funnel. Here are a few examples:

    • “Which of these ideas most resonated with you?”
    • “What are your top three ideas from what we discussed?”

8. Make people “weight” their decisions.

If you’re asking questions to a group of people and want to move the group from brainstorming to action, you often need to know how strongly each person feels about the ideas on the table. Traditional questions like “What do you think we should do next?” often elicit blank stares, so it’s sometimes necessary to make people weight their preferences.

Here are a few weighting systems I’ve found helpful:

    • Everyone gets three votes to cast toward any ideas. They can vote for three different concepts or allocate multiple votes toward one idea they love.
    • Each person must choose their favorite idea, and it must be one they didn’t personally suggest.
    • Each person anonymously stack-ranks their top three options by writing them on a sticky note. Then each person hands in their votes, and you tally the winner. (First-place votes get three points, second-place votes get two points, and third-place votes get one point.)

There will always be good ideas that you cannot pursue, and applying weights to questions acknowledges that fact while moving the group to action steps.

9. Strategically use closed-ended questions to force decisions.

Closed-ended questions (those that can be answered with a mere “yes”/“no” or choosing between limited options) force the person or group to choose between the selections you have created.

Returning to the example of the brainstorming meeting, you would likely want to begin the meeting with open-ended questions and conclude the meeting with closed-ended questions like the following:

    • “It sounds like there is rough consensus around Plan A. All those in favor of Plan A, please raise your hand.”
    • “Kari’s idea garnered the most votes. Does anyone have big reservations with us moving forward with that idea?”

10. Don’t hide answers in your questions.

“The truest way to be deceived is to think oneself more knowing than others.” –François de La Rochefoucauld

Many people utilize questions to not-so-secretly plug their own opinion about something. From a mom asking her son, “Don’t you think that friend is a bad influence?” to a CEO asking an employee, “Why wouldn’t we just [take this course of action]?”, we’re used to hearing people couch their ideas in the form of a question.

Author Michael Bungay Stanier calls this “offering advice with a question mark attached,” and it’s a subtle form of manipulation. Ask legitimate questions — not contrived ones.

11. Apply a rigorous standard to your questions.

Last year, I received some feedback I will never forget. I was pitching a training idea to my CEO, and he asked me how I would determine whether creating the training would be worth my time. I explained that I had begun asking managers, “If I created this training, would you attend the training?”

The CEO immediately called me out: “Bobby, I don’t think you have a rigorous enough standard for the questions you ask.” My ears perked up.

He explained that my question set a low bar and that I should instead ask managers a question like, “What would this training need to look like for you to bring your whole team to the training?” Basic attendance from a single manager wasn’t enough; I needed complete endorsement.

Depending upon the stakes of whatever initiative you’re about to launch, you may need to apply the higher standard of endorsement to the questions you’re asking others. Here are a few examples of endorsement questions:

    • “If you had to contribute $1,000 from your own budget for this project, would you do it?”
    • “How many hours of company time do you think we should put into this all-hands meeting?”
    • “What ROI would we need to see on this software feature to make you feel like it was worth your team’s time to prioritize?”

I’ve had the opportunity to lead hundreds of meetings in my career: strategic planning meetings, 1-on-1s with direct reports, team retrospectives, company offsites, project update meetings, and dozens more.

In those meetings and in my everyday conversations with family and friends, I’ve noticed there is a profound difference in the answers I receive based upon how I ask specific questions.

Questions are the key to unlock insight, wisdom, and creativity. Or in the words of children’s book author Nancy Willard, “Answers are closed rooms; and questions are open doors that invite us in.”

Are you asking the right questions to invite others in?

Bobby Powers


Bobby Powers is the Director of Employee Experience at The Block, a cryptocurrency infoservices company. Bobby reads over 70 books per year and shares his learnings through his website and monthly email newsletter.


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